Twitter beat out Verizon, Yahoo and Amazon for the contract to stream 10 free games during the regular season, while CBS and NBC retained the rights to broadcast the games on television, according to Bloomberg. The terms of the deal were not disclosed but are estimated to set Twitter back less than$1 million per game, according to Re/code.

With the video up top and the Tweets below it, the experience could be "neat," Calacanis said. But Wall Street held back its verdict: Though Twitter shares spiked in early trading, they quickly pared those gains.

"It's not going to be some huge silver bullet that solves all of Twitter's problem," Calacanis said. "What it does speak to is that the community on Twitter is extremely, extremely valuable to content owners."

The social media platform has struggled to get active users compared to competitors such as Facebook. Shares were recently dinged after the company revealed a sequential usership decline in the fourth quarter.

But at $10 million, Twitter could get less than 5 million viewers per game and still make the deal worthwhile, earning back half the money in ad revenue on Periscope streams, Calicanis said.

"I think this is a community play, and the NFL [is] sort of saying, 'Hey, we've got to get this smartphone generation, millennials, to start watching the NFL,'" Calacanis said. "Because frankly, they have too many options. ... And we're losing them, because they don't have cable. They've cut the cords."

(Disclosures: Comcast is the parent of NBCUniversal and CNBC.CNBC parent NBCUniversal is an investor in Re/code's parent Vox Media. Re/code and NBC have a content-sharing arrangement.)